It Depends: Lessons in Technology Leadership

Avoiding shiny object syndrome, encouraging curiosity, and building a system for smart adoption

Every few years, a new wave of technology arrives promising to change everything. Right now, it’s generative AI, but it wasn’t long ago that we were saying the same thing about mobile, cloud, or Web3.

In this episode, Kevin Goldsmith reflects on how leaders can navigate emerging technologies without falling for the hype. Drawing from decades of experience adopting everything from public cloud to AI tooling, he shares how to evaluate what’s worth your team’s attention and when to wait.

Kevin outlines a practical framework for making technology decisions that stick: discover → experiment → evaluate → adopt deliberately. He also explores how to guide both the eager early adopters and the skeptical veterans on your team, turning curiosity into a disciplined system for learning and innovation.

• ConFoo 2026 (https://confoo.ca/en/2026)
• Listener Survey: https://forms.gle/JVeKHsHJKhEM3dvK6
• The book: It Depends: Writing on Technology 2012-2022 (https://itdependsbook.net)
• Your host: Kevin Goldsmith (https://kevingoldsmith.com)